Deuterated DMSO

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Deuterated DMSO
Wireframe of deuterated DMSO DMSO deuterated structure.png
Wireframe of deuterated DMSO
DMSO-d6.jpg
Names
Preferred IUPAC name
[(2H3)Methanesulfinyl](2H3)methane
Other names
Deuterated dimethyl sulfoxide, DMSO-d6
Identifiers
3D model (JSmol)
AbbreviationsDMSO-d6
1237248
ChemSpider
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EC Number
  • 218-617-0
PubChem CID
RTECS number
  • PV6210000
  • InChI=1S/C2H6OS/c1-4(2)3/h1-2H3/i1D3,2D3 Yes check.svgY
    Key: IAZDPXIOMUYVGZ-WFGJKAKNSA-N Yes check.svgY
  • InChI=1S/C2H6OS/c1-4(2)3/h1-2H3/i1D3,2D3
    Key: IAZDPXIOMUYVGZ-WFGJKAKNSA-N
  • InChI=1/C2H6OS/c1-4(2)3/h1-2H3/i1D3,2D3
    Key: IAZDPXIOMUYVGZ-WFGJKAKNEE
  • [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H]
Properties
C2D6OS
Molar mass 84.17 g/mol
Density 1.19 g/cm3 (20 °C)
Melting point 20.2 °C (68.4 °F; 293.3 K)
Boiling point 189 °C (372 °F; 462 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Deuterated DMSO, also known as dimethyl sulfoxide-d6, is an isotopologue of dimethyl sulfoxide (DMSO, (CH3)2S=O)) with chemical formula ((CD3)2S=O) in which the hydrogen atoms ("H") are replaced with their isotope deuterium ("D"). Deuterated DMSO is a common solvent used in NMR spectroscopy.

Contents

Production

Deuterated DMSO is produced by heating DMSO in heavy water (D2O) with a basic catalyst such as calcium oxide. The reaction does not give complete conversion to the d6 product, and the water produced must be removed and replaced with D2O several times to drive the equilibrium to the fully deuterated product. [1]

Use in NMR spectroscopy

C NMR Spectrum of DMSO-d6 13CNMR Spectra of DMSO d6.gif
C NMR Spectrum of DMSO-d6

Pure deuterated DMSO shows no peaks in 1H NMR spectroscopy and as a result is commonly used as an NMR solvent. [2] However commercially available samples are not 100% pure and a residual DMSO-d51H NMR signal is observed at 2.50ppm (quintet, JHD=1.9Hz). The 13C chemical shift of DMSO-d6 is 39.52ppm (septet). [3]

References

  1. ↑ DEapplication 1171422B,Fruhstorfer, Wolfgang&Hampel, Bruno,"Process for the production of hexadeuterodimethyl sulfoxide",published 1964-06-04, assigned to E. Merck A.G.
  2. ↑ Chandak, MS; Nakamura, T; Takenaka, T; Chaudhuri, TK; Yagi-Utsumi, M; Chen, J; Kuwajima, K (22 January 2013). "The use of spin desalting columns in DMSO-quenched H/D-exchange NMR experiments" . Protein Sci . 22 (4). Hoboken, New Jersey, USA: Wiley-Blackwell: 486–91. doi:10.1002/pro.2221. PMC   3610054 . PMID   23339068 . Retrieved 2 June 2023.
  3. ↑ Gottlieb, Hugo E.; Kotlyar, Vadim; Nudelman, Abraham (17 October 1997). "NMR Chemical Shifts of Common Laboratory Solvents as Trace Impurities" . The Journal of Organic Chemistry . 62 (21). Washington, D.C., USA: American Chemical Society: 7512–7515. doi:10.1021/jo971176v. PMID   11671879 . Retrieved 18 June 2011.
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